In high school, I wasn't an ugly duckling, but I wasn't the school beauty either. I was tall, 5 feet 8 inches, and skinny. I measured 35A-28-33. I had some good attributes, as everyone does. Mine were my big brown eyes and my long full reddish blonde hair. My legs are very long, but they were skinny with knobby knees. Twiggy was out of style by then. Girls with nicer curves were in. I was often referred to as "a stick", or "flat as a board". Teenagers can be so thoughtless, uncaring and mean. This made me very self-conscious and my self-esteem was pretty low. I surrounded myself with a self-imposed wall. Needless to say, I never had a date in high school.
The first man came into my life a couple of years after high school. Chris and I met in college. I was having trouble in my organic chemistry class. Chris was an upperclassman who was assigned to tutor me. He was the ideal guy to bring me out of my shell. He was gentle, caring, attentive, handsome, and honest. Even though he had been very popular at his high school, and was still popular in college, he really seemed to care about me. For me, it was love at first sight.
After a couple of tutoring sessions, a miracle happened. Chris asked me out. "I think we need to take a break. Why don't we go grab something to eat?"
I was almost too scared to reply, but I managed to stammer out, "Sure." How eloquent right?
After that night, it became a regular thing. Chris would come to my dorm and help me with my chemistry. Then, we would go to get something to eat or see a movie. It was in a dark theater that he first kissed me. I did not have any experience kissing, but this one was wonderful. I thought my heart would jump out of my chest as my lips opened to his gently questing tongue. I could feel my panties getting wet as the sensations coursed through my body. But, kissing was as far as we went.
After that night, we started making out on every date. As we were kissing one night, I felt Chris' hand on my hip. Slowly, it started moving up my side. As it crossed my belly, I thrust my tongue deeper into his mouth. But, as it gently clasped my tiny boob through my bra, I got worried. I had very small breasts. What if he didn't like them? Without breaking the kiss, I grabbed his hand and pushed it back down to my hip. Chris settled for that.
On the next date, things went further. As we sat in his car, we were kissing and making out. Chris again tried to fondle my boobs through my bra. But, considering how small my boobs were, I wouldn't let him. But, I really liked Chris and did not want to run him off. As his hand moved up and closed over my boob, I pushed his hand downward. Opening my legs slightly, I pushed his hand between them. This was all the encouragement he needed. In a few minutes, he had worked his hand under my skirt and was rubbing my pussy through my panties. I had rubbed my pussy myself, but I had never allowed a boy to do that. This felt entirely different than it did when I masturbated myself.
Soon, I was panting for breath and raising my ass off the seat to meet his hand. He slid his finger under my panties and rubbed over the outside of my wet lips. I was now gasping for breath and thrusting hard against his hand. When he tried to pull my panties down, it took all of my self-discipline, but I stopped him. That was as far as we went that night.
Over the next month or so we went from his rubbing my pussy to where eventually my panties were lying on the floor and his fingers were thrusting in and out of my very wet pussy. That is how I had my very first orgasm, lying in the backseat of a 1968 Camaro. It felt wonderful.
Of course I was also curious about his cock. One night as I was lying in the back seat of his car, bottomless and spread wide to his fingers, I got courageous. I reached down and felt his cock through his jeans. It felt so big, hard and hot. It was the first time I ever touched a cock. As his fingers stroked my pussy, I got hotter and hotter. I grabbed his zipper and pulled it down. Reaching inside I felt the smooth hard skin of his shaft throbbing in my hand. I pulled it out so I could see my first cock. It looked beautiful, but also scary. How could any woman fit something that big up inside her body?
I tentatively began to run my hand along Chris' hard cock, unsure about what I should do. I marveled at how smooth it was. Precum was oozing from the slit in the dome-like head. I took a finger and began rubbing it around the velvety head. I was mesmerized by his dick. I watched as it twitched every time I ran my finger under the head.
Chris stopped rubbing my pussy and sat back to give me more access. As I stroked it I saw another drop of precum form on the tip. Using my thumb, I rubbed it over the head. His moan of delight told me I was doing something right. Watching closely, I started pulling on the shaft as it gleamed in the moonlight.
Soon, I felt it start to twitch and throb harder in my hand. Chris reached down and grasped my hand. "If you don't stop, I'm going to come all over you." He gasped.
This intrigued me even further. Of course I knew that men squirted cum out of their cocks, but since this was the first time I had seen one, I had never witnessed a guy cumming. I wanted to make Chris cum.
Reaching down into my purse, I bought out a handkerchief. My mother had always insisted that I carry one with me. Somehow, I did not think this was the reason she had in mind. Placing it over the head of his cock, I wrapped my hand around it and started pumping his cock again.
Soon, he was arching his hips up to meet my hand. His gasps became moans as he neared climax. Suddenly he stiffened as I felt his warm cum flooding out of his cock and filling my handkerchief. There was a lot of it. I continued to pump his cock until he reached down and stopped me. I could feel my juices flooding out of me as I realized that I had just given my first handjob.
The next several dates ended with me giving Chris a handjob. But, we both wanted more. One Saturday night, we went to a drive-in movie with one of my classmates, Carol, and her boyfriend, Ed. During the movie, Chris and I were kissing and making out. He tried to rub my pussy through my jeans, but I was afraid my friends would see us. Looking over the seat at Carol, I saw Ed had his hand up under her skirt. His arm was moving in a steady rhythm as he obviously pumped his fingers in and out of her pussy. Her head was thrown back on the seat and she had one hand inside her blouse pulling on her nipple. As I watched, her, back arched off the seat as she climaxed.
Ed looked at m and grinned. When Carol opened her eyes, she saw me watching them. She smiled at me and then reached down to Ed's crotch. I watched as Carol unzipped her boyfriend's pants. I felt Chris unzip my own jeans as Carol pulled Ed's cock out into the dim light in the backseat. It was the only cock I had ever seen other than Chris'. It looked shorter than the one I was used to, but it was thicker. Absentmindedly, I raised my hips and allowed Chris to pull my jeans down and completely off.
My pink panties were not visible to Carol and Ed in the backseat. But, Chris did not waste any time pushing his fingers inside my panties and up into my very wet pussy. I opened my legs slightly to make it easier for Chris to finger me as I watched Carol stroke Ed's hard cock.